Synthesis of symmetrical 4,4'- and 6,6'- bis(D-glucose)-based probes as tools for the study of D-glucose transport proteins

Article abstract of DOI:10.1016/S0040-4039(99)01241-1

Two glucose moieties have been linked from positions -4 or -6 and hydrophobic groups have been placed symmetrically between the hexose moities. To crosslink glucose and obtain 6,6'-probes, advantage has been taken of the unusual reactivity of D-glucurono-γ-lactone with amines. To obtain 4,4'- linked probes, crosslinking via reductive amination has been used. The affinities of these probes for the glucose carrier have been determined and found to be 20 to 200 times that of D-glucose.